Estia Villas - Vacation Rentals in Hillsmere Shores
House
9.8
(
59 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating -
Balcony/Terrace -
Pet Friendly -
Kitchen
US $765
/Night
7 Nights - $5,355
10.0
(
3 Reviews
)
6 Bedrooms
5 Bathrooms
18 Guests
5597.23 ft²
-
Spa -
Fireplace/Heating
-
Pool -
View
US $955
/Night
7 Nights - $6,682
9.2
(
24 Reviews
)
1 Bedroom
1 Bathroom
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $392
/Night
7 Nights - $2,744
House
9.6
(
19 Reviews
)
4 Bedrooms
3 Bathrooms
6 Guests
3000 ft²
-
Fireplace/Heating
-
Ocean View -
Balcony/Terrace
-
View
US $730
/Night
7 Nights - $5,110
House
9.8
(
72 Reviews
)
4 Bedrooms
4 Bathrooms
14 Guests
3000 ft²
-
Oceanfront -
Hot Tub -
Fireplace/Heating
-
Ocean View
US $871
/Night
7 Nights - $6,097
Cottage
10.0
(
174 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
950 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $352
/Night
7 Nights - $2,462
House
10.0
(
143 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1100 ft²
-
Private Pool -
Fireplace/Heating
-
Pool
-
Ocean View
US $651
/Night
7 Nights - $4,557
House
10.0
(
99 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $469
/Night
7 Nights - $3,284
See More Hillsmere Shores Vacation Rentals
Luxury Places to Stay in Hillsmere Shores
Over 387+
Luxury Places to Stay in or Near Hillsmere Shores
House
10.0
(
27 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2900 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $2,931
/Night
7 Nights - $20,517
House
6 Bedrooms
5 Bathrooms
12 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $2,929
/Night
7 Nights - $20,506
House
10.0
(
10 Reviews
)
7 Bedrooms
4 Bathrooms
14 Guests
4000 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $2,241
/Night
7 Nights - $15,684
House
9.6
(
19 Reviews
)
7 Bedrooms
4 Bathrooms
26 Guests
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $2,203
/Night
7 Nights - $15,421
House
6 Bedrooms
5 Bathrooms
12 Guests
452.08 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Parking
US $2,106
/Night
7 Nights - $14,742
House
10.0
(
12 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2500 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $2,083
/Night
7 Nights - $14,579
House
6 Bedrooms
7 Bathrooms
14 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Air Conditioner -
Internet
US $1,934
/Night
7 Nights - $13,537
House
6 Bedrooms
4 Bathrooms
12 Guests
6500 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $1,889
/Night
7 Nights - $13,225
Find More Hillsmere Shores Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Hillsmere Shores
Over 57+
Top-Rated Vacation Rentals with a Pool in or Near Hillsmere Shores
Condo
10.0
(
29 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
1001 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $575
/Night
7 Nights - $4,026
Condo
10.0
(
13 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Pool
-
Ocean View
-
Balcony/Terrace
US $506
/Night
7 Nights - $3,539
Condo
10.0
(
9 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Pool
-
Kitchen
-
Parking
US $346
/Night
7 Nights - $2,423
Condo
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
759 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $560
/Night
7 Nights - $3,921
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
6 Guests
527.43 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
View
US $436
/Night
7 Nights - $3,052
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
600 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $370
/Night
7 Nights - $2,592
House
9.0
(
2 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
-
Private Pool
-
Spa
-
Fireplace/Heating
-
Pool
US $1,517
/Night
7 Nights - $10,622
Apartment
9.0
(
1 Review
)
1 Bedroom
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Parking
US $218
/Night
7 Nights - $1,526
Pet-Friendly Vacation Rentals in Hillsmere Shores
Over 113+
Pet-Friendly Vacation Rentals in or Near Hillsmere Shores
House
10.0
(
47 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $614
/Night
7 Nights - $4,299
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
2335.77 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Parking
-
Air Conditioner
US $664
/Night
7 Nights - $4,645
House
9.6
(
51 Reviews
)
4 Bedrooms
4 Bathrooms
14 Guests
3000 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
US $896
/Night
7 Nights - $6,272
House
10.0
(
33 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $579
/Night
7 Nights - $4,054
House
10.0
(
9 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1316 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $604
/Night
7 Nights - $4,229
Apartment
10.0
(
9 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
678 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $537
/Night
7 Nights - $3,761
House
10.0
(
5 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
23541 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $516
/Night
7 Nights - $3,610
House
10.0
(
4 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
2500 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $767
/Night
7 Nights - $5,366
See More Pet-Friendly Vacation Rentals in Hillsmere Shores on PetFriendly.io
Large Vacation Homes & Villas in Hillsmere Shores
Over 110+
Large Vacation Homes & Villas in or Near Hillsmere Shores
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
10 Guests
1485.42 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Parking
-
Air Conditioner
US $535
/Night
7 Nights - $3,742
House
10.0
(
26 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
-
View
US $878
/Night
7 Nights - $6,143
House
6 Bedrooms
3 Bathrooms
10 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $537
/Night
7 Nights - $3,757
House
Steps to Downtown Annapolis & Spa Creek from Stunning Craftsman with Game Room, Parking and Backyard
10.0
(
21 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
3489 ft²
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
US $875
/Night
7 Nights - $6,123
House
10.0
(
11 Reviews
)
6 Bedrooms
6 Bathrooms
15 Guests
3498 ft²
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $1,883
/Night
7 Nights - $13,184
House
10.0
(
6 Reviews
)
5 Bedrooms
2 Bathrooms
9 Guests
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Air Conditioner
US $617
/Night
7 Nights - $4,317
House
10.0
(
2 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
1800 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $812
/Night
7 Nights - $5,685
House
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
10 Guests
-
Fireplace/Heating
-
Ocean View
-
View
-
Kitchen
US $1,060
/Night
7 Nights - $7,423
See More Family Vacation Rentals in Hillsmere Shores on FVR
Wheelchair Accessible Vacation Homes in Hillsmere Shores
Over 11+
Wheelchair Accessible Vacation Homes in or Near Hillsmere Shores
Condo
1 Bedroom
1 Bathroom
4 Guests
526 ft²
-
Private Pool
-
Oceanfront
-
Fireplace/Heating
-
Pool
US $624
/Night
7 Nights - $4,369
Condo
9.8
(
59 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
991 ft²
-
Balcony/Terrace
-
View
-
Kitchen
-
Air Conditioner
US $489
/Night
7 Nights - $3,423
Condo
9.2
(
10 Reviews
)
1 Bedroom
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $280
/Night
7 Nights - $1,962
House
4 Bedrooms
3 Bathrooms
14 Guests
4300 ft²
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
-
View
US $2,280
/Night
7 Nights - $15,960
Condo
1 Bedroom
1 Bathroom
2 Guests
-
Pool
-
Kitchen
-
Air Conditioner
-
Child Friendly
US $260
/Night
7 Nights - $1,820
Condo
1 Bedroom
1 Bathroom
2 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Wheelchair Accessible
US $96
/Night
7 Nights - $672
Condo
1 Bedroom
1 Bathroom
2 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $79
/Night
7 Nights - $553
Condo
10.0
(
9 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Parking
US $344
/Night
7 Nights - $2,410
Hillsmere Shores Vacation Rentals and Airbnb Places to Stay Under $200
Over 23+
Hillsmere Shores Vacation Rentals and Airbnb Places to Stay Under $200
New
Apartment
1 Bedroom
2 Bathrooms
90 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $194
/Night
7 Nights - $1,356
House
10.0
(
17 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Kitchen
-
Child Friendly
-
Barbecue/Outdoor Cooking -
Security/Safety
US $152
/Night
7 Nights - $1,064
Apartment
9.4
(
3 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Air Conditioner
US $119
/Night
7 Nights - $833
House
9.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $189
/Night
7 Nights - $1,324
Apartment
4.9
(
14 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1500 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $145
/Night
7 Nights - $1,015
Apartment
4.8
(
29 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
950 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $177
/Night
7 Nights - $1,239
Apartment
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $191
/Night
7 Nights - $1,337
Cottage
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Air Conditioner
US $160
/Night
7 Nights - $1,117
Instantly Bookable Vacation Homes in Hillsmere Shores
Over 175+
Instantly Bookable Vacation Homes in or Near Hillsmere Shores
Apartment
10.0
(
65 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1000 ft²
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $386
/Night
7 Nights - $2,701
House
9.8
(
11 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
US $457
/Night
7 Nights - $3,196
House
10.0
(
60 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $592
/Night
7 Nights - $4,142
House
10.0
(
41 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $370
/Night
7 Nights - $2,592
House
10.0
(
34 Reviews
)
3 Bedrooms
2 Bathrooms
5 Guests
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Air Conditioner
US $272
/Night
7 Nights - $1,903
House
10.0
(
24 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $547
/Night
7 Nights - $3,826
House
10.0
(
16 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $409
/Night
7 Nights - $2,860
House
10.0
(
8 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1650 ft²
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
-
View
US $459
/Night
7 Nights - $3,215
About Hillsmere Shores Vacation Rentals
With more than 396 Hillsmere Shores vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Hillsmere Shores.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Hillsmere Shores, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Hillsmere Shores. Places to stay near Hillsmere Shores are 1254.96 ft² on average, with prices averaging US $703 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Hillsmere Shores with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Hillsmere Shores
| Type | Count |
|---|---|
| Vacation Homes | 308 |
| Holiday Apartments | 39 |
| Cottages | 13 |
| B&B | 1 |
Use these Quick Filters to Find a Vacation Rental in Hillsmere Shores
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Hillsmere Shores.
Weather in Hillsmere Shores
View the weather forecast for Hillsmere Shores before booking your Hillsmere Shores Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Hillsmere Shores, MD
Estiavillas offers a large selection of top attractions around Hillsmere Shores. Research things to do on your vacation before you visit Hillsmere Shores.
U.S. Naval Academy
Six Flags America
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Show Place Arena
Bowie State University
Chesapeake Beach Water Park
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Rod n Reel Charter Fishing
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
Fort George G. Meade
St. Michaels Winery
Prince George's Community College
Queenstown Premium Outlets
Annapolis Maritime Museum
Hillsmere Shores Vacation Rental Frequently Asked Questions
How many vacation rentals have private pools in Hillsmere Shores?
There are 19 vacation rentals with private pools near Hillsmere Shores. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Hillsmere Shores are best for families?
If you are looking for a family-friendly vacation home in Hillsmere Shores, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hillsmere Shores:
How many vacation rentals are available in Hillsmere Shores?
Currently, the total number of properties listed in 2026 is over 396 in the Hillsmere Shores area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Hillsmere Shores.
